Table 2. Cooperative effects of boronic acid–DMAPO on the dehydrative condensation reaction a .
| |||
| Entry | ArB(OH)2 | Yield b , c (%) of PhEtCHCONHBn | Yield b , d (%) of PhCONHBn |
| 1 | 2 | 99 [<5] | 97 [<5] |
| 2 | PhB(OH)2 | <5 [<5] | <5 [<5] |
| 3 | 4b | 92 [<5] | 20 [8] |
| 4 | 3 | 7 [15] | 80 [95] |
a0.5 mmol of carboxylic acid and 0.5 mmol of benzylamine were used in the presence of 5 mol% of ArB(OH)2 and 0 or 5 mol% of DMAPO.
bThe results when both catalysts were used are shown. For comparison, the results without DMAPO are shown in brackets.
cConditions: fluorobenzene (bp. 85 °C), 17 h.
dConditions: toluene (bp. 110 °C), 4 h.